Why I started ChooseASquare

How did you get started running pools?

I’ve been running fundraising pools for baseball teams for close to ten years now, mainly squares games. Along the way, someone introduced me to series squares and formats that pay out for each game in the NCAA tournament. I loved those ideas and carried that thinking into NFL pools, too.

More recently, I’ve been running annual pools for our high school Dugout Club. The money helps cover travel, equipment, food, and all the other things a baseball program needs when it relies on donations to operate.

When you’re organizing one of these pools, you know what the money is helping pay for. That makes the work worth doing. But it doesn’t make the work any less work.

What made you decide to build your own platform?

I had used other pool platforms for years, and I kept getting frustrated with the interfaces and the amount of manual work left for me to do. I also wanted an experience that felt more appropriate for the team families and supporters participating in our fundraisers, without so much unrelated advertising and gambling-related clutter.

Eventually, I thought, “I love web technology. I love building platforms. I know these problems because I’m dealing with them myself. Why don’t I build something better?”

That’s where ChooseASquare started. I wanted a platform I would actually want to use as the commissioner.

What was the biggest headache?

Payment tracking. Easily.

I was keeping Google Sheets and building fancy display formulas to track hundreds upon hundreds of payments each year. Meanwhile, I was coordinating with our treasurer, who had the Venmo access. Keeping the pool information, the spreadsheet, and the payment information in sync was a constant challenge.

Even with all that effort, it was still difficult. That experience is a big reason payment tracking is a core part of ChooseASquare. Forwarded receipts match themselves against your list, so “who actually paid?” stops being a weekly job. And Payout Assist does the same for the other end, when it’s time to pay the winners.

We still have work to do on it. Longer term, we may even let organizations connect their own merchant accounts and process charges directly. That’s a possibility we’re considering, not a feature I’m promising today. But the problem we’re trying to solve is very real to me.

The 300 Club has a much older connection for you. What’s the story there?

That goes all the way back to when I was a kid. Our organization ran a 300 Club fundraiser that brought in about $30,000 a year and paid out about $12,000 in prizes. It was an amazing fundraiser, and it stuck with me.

I wasn’t seeing that concept in the platforms I was looking at, and I wanted to bring it into ChooseASquare. It runs here as Century Club.

It also got me thinking beyond a single game or a single fundraiser. How could we build something organizations could use throughout the year, with enough flexibility to run the contests and fundraisers that work for their community?

Beyond collecting money, what did you need to understand about a fundraiser?

I wanted to know which players were actually helping make it successful. You could see the overall results, but tracking who was bringing in support was another thing I was always trying to piece together.

That’s why we’ve put so much attention into seller tracking links and goals. I want an organization to be able to connect the support coming in to the player or seller who helped bring it in, and see how that person is doing toward their goal.

That gives you a way to recognize people’s efforts and see where someone might need a little encouragement or help. When you’re asking a whole team to participate in a fundraiser, you need a clear picture of how it’s going.

Why is custom branding such a priority for you?

It’s crucial. If someone follows a link to support your team or organization, I want them to immediately recognize where they are and feel comfortable participating. Your name, your logo, your colors. It should feel like your fundraiser.

Too often, the experiences I’d used felt like an organization’s name dropped onto a generic page. I wanted something we could be proud to send to parents, grandparents, friends, and local businesses. It should look reputable, make it clear who you’re supporting, and make it easy to take part.

And I care about how it looks on paper, too. My family still prints our pools and brackets and tapes them to the fridge during the big games. Those printouts become part of the fun. I want them to look nice and be easy to read. If it’s going to live on the fridge for the tournament, the formatting deserves some attention.

Where do sponsors fit into that?

Sponsorships and advertising are fundamental to fundraising for a lot of organizations. Businesses help make these programs possible, and you want to recognize them in front of the people who are participating and supporting the team.

That’s why sponsor placement matters to me. I want organizations to have space to showcase their sponsors as part of their own branded fundraiser. As people share it and come back to follow the competition, there’s an opportunity for those sponsors to reach a bigger audience.

The advertising that frustrated me on other platforms felt disconnected from why we were there. Giving an organization a way to recognize the businesses supporting its program serves a purpose I care about.

Have you always been interested in technology?

Since I was a kid, when computers were just becoming a thing. Yes, I’m that old.

I taught myself programming and have been tinkering with platforms ever since. One project was a site called Face Value Or Less. It’s no longer around, but it was a marketplace where people could resell tickets for no more than face value, with a particular focus on Dave Matthews Band tickets.

I’ve always liked building things that solve a practical problem. And if there’s something tedious that technology could automate, I have a hard time leaving it alone.

ChooseASquare brings those interests together: building technology, organizing competitions, and taking some of the repetitive work off people’s plates.

How did baseball fundraising turn into baking shows and baby arrival contests?

My family makes a competition out of everything.

We’ve always played pick’em and bracket games. We also turn shows like The Great British Baking Show into family competitions. And if there’s a baby on the way, of course we’re going to guess when the baby will arrive.

As I was building ChooseASquare, I kept seeing more things we could use it for. Now my whole family has one platform for different kinds of contests throughout the year.

Fundraising is still a big part of why I care about this. But sometimes you just want a fun competition with your family, friends, or coworkers. I want the platform to work for that, too.

With so many ideas, how do you keep the platform easy to use?

Honestly, that’s something we’ve had to learn and correct.

I kept thinking of features and customizations we could add, and the scope got away from me a little. We heard loud and clear that setup was too complicated and took too long. Some of the less-used functionality had bugs, too.

We’ve been finishing a major overhaul to simplify the experience. The goal is to make the basics something you can set up in a few clicks, while still letting people dig deeper and customize if they want to.

Someone running a straightforward pool should have an easy path through setup. Someone with a specific format in mind should have room to make it their own. Getting that balance right is a big focus for us.

What do you want people to know about where ChooseASquare is today?

We have work to do. We’ve made mistakes, and I’m comfortable acknowledging that. What matters is that we listen, correct quickly, and keep making it better.

I’m using this for my own pools and family contests, so I care about how it works. But other commissioners bring ideas and experiences I wouldn’t have thought of on my own. That feedback helps us figure out what needs attention and where we can make things easier.

We’re fine-tuning it one day at a time.

What plans are still in the works for ChooseASquare?

We’re expanding the reality TV competitions, which is something I’m especially excited about because my family loves turning something as simple as watching a series into a game. The Great British Baking Show is a perfect example. Having your own picks and a little friendly competition gives everyone another reason to look forward to watching together.

It makes for some great family moments. And it even gives my teenagers a legitimate reason to have their phones in their hands while we’re watching. At least this time, we’re all playing the same game.

On the fundraising side, we have more modules coming, including simple fundraisers built around reaching a dollar goal and activity-based fundraisers like hop-a-thons. I want organizations to have more ways to raise money throughout the year, whether or not there’s a sporting event involved.

We also have two sister sites we’re planning to launch in the near future. SignupRally.com will focus on volunteer and donation signups. It will eventually replace ChooseASquare’s Signups module, while remaining available as part of our fundraising package.

Then there’s TournaPilot.com, which we’re building for organizations running tournaments. I’ve spent a lot of time on that side of things, too, and I have plenty of ideas about what would make a tournament organizer’s life easier. I want it to be the kind of platform those organizations dream of having, but we’ll save that Q&A for another day!

What would make you feel like you’ve succeeded?

I want someone to finish running their first contest and say, “Man, that WAS easy.”

That’s the goal. Whether they’re raising money for a baseball program or competing with their family over a baking show, I want them to enjoy it, and to feel good about doing it again.